#CheapWeek: 4/27 – 5/3

4/27 – NYC Bagel and Soupbox


Monday’s are hard. I like to make them better with delicious food. So I started my day at NYC Bagel Deli with a savory bagel and a copious amount of cream cheese for under $3. Although I brought a lunch, I decided I was past due for a visit to Soupbox. Soupbox is awesome because you get generous samples of as many flavors as you want. And you can mix two flavors. Bread comes free on the side!

4/28 – CP Trade Show at Navy Pier


As mentioned in previous posts, I work for an awesome company called Social Media Beast. Our sister company, Concierge Preferred (CP), has a lot of connections in Chicago, and brings them all together for an annual trade show. We all attended the show on Tuesday and had an amazing time connecting with representatives from participating businesses. We even raked in some first-class freebies. Here’s what I walked away with:

-Free “Second City” tickets
-No cover passes to Howl at the Moon (and the dueling pianos at the event played my song request!)
-Free indoor skydiving session in Rosemont
-Free Navy Pier ferris wheel admission
-Free Chicago Segway tour tickets

Giving a Medieval Times knight a Social Media Beast tattoo

I’m trying to decide if I should keep these freebies or share them with you, my lovely readers, as giveaways. Let me know if any of the above are of interest to you in the comments 🙂

Besides the above freebies, there was plenty of food and drink from Chicago’s top restaurants. The best part of all? The event is free, so you better make sure to get your Cheap Ass there next year! Just make sure to show some love if a business there impresses you.

4/29 – James Beard event at Mariano’s


The Mariano’s in the West Loop has some pretty cool events, and I’ve been to two in the past month. On Wednesday, I invited a couple of girlfriends to a happy hour featuring Blackbird’s mixologist, Kyle Davidson. Light appetizers (but lots of cheese) were served with unlimited craft cocktails. The event concluded with Blackbird’s mixologist teaching us how to make two specialty cocktails. This was well worth the $20, and was one of the more affordable ways to celebrate the James Beard Awards coming to Chicago.

I ended the night by redeeming my BOGO coupon to Noodles & Company for their new Buff Bowls. So glad I did! $9 covered a relatively healthy lunch for the next two days.

4/30 – Haircut at Civello

Photo Credit: Civello’s Website

I’ve been desperately in need of a haircut, and I usually time it out so I can take care of it when I’m home in the suburbs. But, split ends are split ends. I took a chance at a new place. I’m honestly not very high maintenance with my hair – I’m brush and go. As far as haircuts, a simple trim will usually do the job for me, so I decided to check out a beauty school a few blocks away from work – Civello. They happened to be running a Groupon deal for a $15 haircut. I was pleasantly surprised with my experience. The haircut (which was awesome) included an aromatherapy scalp massage, a deep conditioning treatment, and a cut. I ended up buying some product (detangler) because it all smells so damn good. They also gave me some curly hair treatment samples to take home! I made sure to tip my hairstylist well as you ALWAYS should when using a Groupon.

5/1 – Henry’s Swing Club

Henry's Swing Club

I recently won a poetry writing contest at Henry’s Swing Club for 5 free sliders, 7 free cocktails, and 5 free giant pretzels. My haiku really captured the spirit of the bar… read it here.

5/2 – Kentucky Derby and Rioja Wine and Tapas Festival

I’m pretty good at betting on horse racing, so I love events like the Kentucky Derby. It’s a good excuse to dress up and get drunk. And maybe win some money.


This particular Kentucky Derby Saturday was especially cool because I received free tickets to the Rioja Wine and Tapas Festival. I expressed an interest in covering the event for Choose Chicago, told the organizer how obsessed I am with Spanish culture, and she hooked up it!


I had an amazing time chatting with the people in charge of the event, drinking delicious Rioja wines (reds I can actually enjoy), and sampling tapas prepared by chefs from all over the United States.


Afterwards, I checked out Joe’s on Weed Street, which was completely blocked off for the Derby. And it was packed. Unfortunately, I was a little late in making my bets, but I still had a good time enjoying the first nice weather we’ve had in a while with a tall, cold one.


I finished the night off at the NFL Draft Town – a free fan festival to complement Chicago hosting the NFL Draft. Chicago is such an amazing city. A lot of great things have been happening here and we all reap the benefits.

5/3 – Relaxing

No major Cheap Ass hustling today. It’s been a long week, and I spent the day sleeping in, making a big breakfast, going to the gym, writing blogs, and eating dinner with the new Game of Thrones. Excited to see what the new week brings in!

By Maddy Osman

Maddy is the founder of Chicago Cheap Ass. She loves to read, travel, cook, and play with her adorable dog Leonidas.

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